Journal Article Copper-Catalyzed gamma-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes

Yasuda, Yuto  ,  Nagao, Kazunori  ,  Shido, Yoshinori  ,  Mori, Seiji  ,  Ohmiya, Hirohisa  ,  Sawamura, Masaya

21 ( 27 )  , pp.9666 - 9670 , 2015-06-26 , Wiley-Blackwell
The scope of the copper-catalyzed coupling reactions between organoboron compounds and allylic phosphates is expanded significantly by employing triphenylphosphine as a ligand for copper, allowing the use of secondary alkylboron compounds. The reaction proceeds with complete gamma-E-selectivity and preferential 1,3-syn stereoselectivity. The reaction of gamma-silicon-substituted allylic phosphates affords enantioenriched alpha-stereogenic allylsilanes.

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